benzoic acid (-)-(3S,4S,5R)-5-(tert-butyldiphenylsilanyloxymethyl)-4-fluorotetrahydrothien-3-yl ester | 917377-29-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: benzoic acid (-)-(3S,4S,5R)-5-(tert-butyldiphenylsilanyloxymethyl)-4-fluorotetrahydrothien-3-yl ester
• CAS: 917377-29-8
• 化学式: C₂₈H₃₁FO₃SSi
• 分子量: 494.702
• InChiKey: TZZKSXHKBZNMIP-CYXNTTPDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.24
• 重原子数：
  34.0
• 可旋转键数：
  7.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  35.53
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  benzoic acid (-)-(3S,4S,5R)-5-(tert-butyldiphenylsilanyloxymethyl)-4-fluorotetrahydrothien-3-yl ester 在 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 4.0h， 以96%的产率得到(+)-(3S,4S,5R)-5-(tert-butyldiphenylsilanyloxymethyl)-4-fluorotetrahydrothien-3-ol
  参考文献：
  名称：

  Design, synthesis, and biological evaluation of novel iso-d-2′,3′-dideoxy-3′-fluorothianucleoside derivatives

  摘要：

  Novel iso-D-2',3'-dideoxythianucleoside derivatives 1-4 were designed and asymmetrically synthesized as a bioisostere of lamivudine to search for new anti-HIV agents. The information about using sulfur participation occurred on DAST fluorination and Mitsunobu reaction will be of great help in synthesizing sulfur-containing compounds. Final compounds 1-4 were evaluated against HIV-1 and 2, HSV-1 and 2, EMCV, Cox. B3, VSV, FluA (Taiwan), FluA (Johan.), FCV, and FIR Only cytosine analogue 3 showed a potent anti-VSV activity (EC50 = 9.43 mu g/mL). This result implies that iso-2',3'-dideoxy sugar templates might play a role of a sugar surrogate of nucleosides for the development of anti-RNA virus agent. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.09.066
• 作为产物：
  描述：

  benzoic acid (-)-(3S,4S,5R)-5-(tert-butyldiphenylsilanyloxymethyl)-4-hydroxytetrahydrothien-3-yl ester 在 4,4'-二氨基二苯乙烯-2,2'-二磺酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以88%的产率得到benzoic acid (-)-(3S,4S,5R)-5-(tert-butyldiphenylsilanyloxymethyl)-4-fluorotetrahydrothien-3-yl ester
  参考文献：
  名称：

  Design, Enantiopure Synthesis, and Biological Evaluation of Novel ISO-D-2′,3′-Dideoxy-3′-Fluorothianucleoside Derivatives as a bioisostere of Lamivudine

  摘要：

  Novel isoD-2',3'-dideoxythianucleoside derivatives 1-3 were designed and asymmetrically synthesized to search for new anti-HIV agents. Final compounds 1-3 were evaluated against a variety of viruses including HIV-1 and 2. Only cytosine analog 3 showed a potent anti-VSV activity (EC50 = 9.43 mu g/mL). This result implies that iso 2',3'-dideoxy sugar templates might play a role of a sugar surrogate of nucleosides for the development of anti-RNA virus agent.

  DOI：

  10.1080/15257770701506426